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Hibernian were promoted to the league after winning the 1998–99 First Division by a 23 point margin. They replaced Dunfermline Athletic who were relegated after a three-season stint in the top flight, finishing bottom of the league the previous season.

The 1999–2000 Scottish Premier League was won by Rangers for the second successive year, finishing 21 points ahead of nearest rivals Celtic. As champions, Rangers qualified for the Champions League while Celtic and third-placed Hearts qualified for the UEFA Cup.

As the SPL was being expanded to 12 teams, the bottom finishing side were to face the second and third finishing sides from the First Division, in a three team play-off. However, due to Falkirk's stadium (Brockville Park) having fewer than the SPL minimum required 10,000 seats, the playoff did not take place. Therefore, bottom-placed Aberdeen were spared relegation and Dunfermline were promoted automatically as the First Division runner-up.[25] Aberdeen appeared in both the League Cup and Scottish Cup final, but lost both to Celtic and Rangers, respectively. However, as Scottish Cup runners-up, they also qualified for the following season's UEFA Cup.

Celtic entered the season under new management with former Liverpool player John Barnes taking charge in June 1999.[26] It proved to be a brief and unsuccessful reign, however, after being sacked in February 2000, ten points behind Rangers in the league, and in the wake of a Scottish Cup defeat to First Division Inverness Caledonian Thistle.[24]

On 20 October 1999, Aberdeen and Motherwell played out a match which finished in a 6–5 victory for Aberdeen at Fir Park.[27] This was the record for the highest-scoring match in Scottish Premier League history, until Motherwell and Hibernian played out a 6–6 draw in May 2010, also at Fir Park.

Rangers secured the league title on 22 April 2000, after Celtic drew 1–1 with Hibernian at Celtic Park, leaving Celtic with a 17-point deficit with only 5 matches left to play.[1]

Source: Soccerbase1 ^ The home team is listed in the left-hand column.Colours: Blue = home team win; Yellow = draw; Red = away team win.For coming matches, an a indicates there is an article about the match.

Source: Soccerbase1 ^ The home team is listed in the left-hand column.Colours: Blue = home team win; Yellow = draw; Red = away team win.For coming matches, an a indicates there is an article about the match.